Synthesis of novel C-4'-spiro-oxetano-α-L-ribonucleosides

Rajesh Kumar; Manish Kumar; Ankita Singh; Neetu Singh; Jyotirmoy Maity; Ashok K Prasad

doi:10.1016/j.carres.2017.04.018

Synthesis of novel C-4'-spiro-oxetano-α-L-ribonucleosides

Carbohydr Res. 2017 Jun 5:445:88-92. doi: 10.1016/j.carres.2017.04.018. Epub 2017 Apr 19.

Authors

Rajesh Kumar¹, Manish Kumar¹, Ankita Singh¹, Neetu Singh¹, Jyotirmoy Maity¹, Ashok K Prasad²

Affiliations

¹ Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India.
² Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India. Electronic address: ashokenzyme@gmail.com.

PMID: 28460347
DOI: 10.1016/j.carres.2017.04.018

Abstract

The synthesis of novel C-4'-spiro-oxetano-α-L-ribonucleosides T and U in 39 and 45% overall yields have been achieved from 2',3',5'-tri-O-acetyl-4'-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosylthymine and 2',3',5'-tri-O-acetyl-4'-C-p-toluenesulfonyloxymethyl-β-D-xylofuranosyluracil, respectively. Both the tosylated nucleoside precursors have been synthesized following recently developed Novozyme^®-435 catalyzed methodology.

Keywords: Biocatalysis; Diastereoselectivity; Spiro-oxetano-α-L-ribonucleosides.

MeSH terms

Chemistry Techniques, Synthetic
Ribonucleosides / chemical synthesis*
Ribonucleosides / chemistry*
Spiro Compounds / chemistry*

Substances

Ribonucleosides
Spiro Compounds